Yankees: 3 pitchers Brian Cashman should overpay for in a trade

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The Yankees should do (almost) whatever it takes to acquire one of these pitchers via trade.

If the New York Yankees are going to be stingy with money this offseason, then there’s no reason they shouldn’t be liberal with moving top players in their farm system in order to trade for MLB-ready talent. After all, that’s currency 1a. after actual cash.

There are plenty of additions the Bombers need to make, but once again, pitching is their greatest need and the free agent market doesn’t possess many answers for them. But the trade market? That’s an entirely different story, especially if you have the resources to pay up for a momentous acquisition.

And the Yankees do. They have one of the best talent pipelines in all of baseball, which countless other organizations value more greatly than anything else because there aren’t many who possess the spending power of the Yankees. Others are just plain cheap, but whatever works! If prospects can get the deal done and capture a World Series for the Yanks in the next couple years, it’ll be well worth it.

These teams may not be keen on trading these star pitchers, but if general manager Brian Cashman kicks the door down with an offer that’s almost impossible to turn down, the Yankees can flip this offseason on its head. Here are three pitchers New York should be more than willing to overpay for if the opportunity arises.

ATLANTA, GA – OCTOBER 01: Luis Castillo #58 of the Cincinnati Reds (Photo by Todd Kirkland/Getty Images) /

3. Luis Castillo

If Trevor Bauer leaves the Reds, the Yankees should call them about Luis Castillo.

If the Cincinnati Reds are honest with themselves, they’ll realize 2020 was their only legitimate chance at making a World Series run. They had a three-headed rotation led by NL Cy Young winner Trevor Bauer and he was followed by Luis Castillo and former Yankees outcast Sonny Gray. But they lost in the Wild Card round against the Braves because they couldn’t hit a baseball.

Bauer is more than likely to leave, too. He’ll be signing a lucrative deal elsewhere, which leaves Cincy with Castillo and Gray. It’s still possible to contend with that … if you can hit. But the Reds cannot hit, so why not trade Castillo in the offseason for a combo of top prospects and controllable MLB talent and then wait for the summer deadline when perhaps the pandemic ends and other teams are willing to acquire some big contracts (which would make Mike Moustakas and Nick Castellanos a lot easier to move).

We’re not making up trade packages for these because there are all different kinds, but Cashman should be willing to splurge for a guy like Castillo, who is under club control through 2023 and has ace potential, as evidenced by his 578 punchouts and 3.62 ERA in 90 career starts. And he had an impressive postseason debut against the Braves!

The soon-to-be 28-year-old is sliding into his prime and he could be Gerrit Cole’s right-hand man for the next three years. Keep Jasson Dominguez, leave everyone else on the table. See what happens.

Max Scherzer of the Washington Nationals. (Photo by Rob Carr/Getty Images) /

2. Max Scherzer

The Yankees should call up the Nationals and go for it all in 2021.

I’m sick of pitching this, because it couldn’t be more obvious. The Washington Nationals have simply lost too many players to make another World Series run, so there’s little need for them to have all of Max Scherzer, Stephen Strasburg and Patrick Corbin under contract. Truth be told, they’re stuck with Stras and Corbin until further notice.

But Scherzer? The 36-year-old is under contract for one more year at $34 million and the price could be lowered for his services after a lackluster 2020 (3.74 ERA, 1.38 WHIP). This is a go-for-it-all in 2021 move, and what’s not to like about it? It’s a short-term financial commitment and you’re getting a bonafide second ace. Unless there’s an injury, there will be no problem with putting together the postseason rotation.

Scherz is pretty damn good in the postseason, too. Across 22 career games (18 starts), the three-time Cy Young winner is 7-5 with a 3.38 ERA, 1.13 WHIP and 137 strikeouts in 112 innings. We’re salivating. The Yankees can cry about money all they want, but this move (if possible) is arguably their best chance to take home a World Series during this current window.

If they’re worried about spending in the short term, then what’s their long-term outlook with everybody approaching arbitration or free agency? Nothing is going to be cheap! Just live with giving people paper in order to succeed.

Kyle Hendricks #28 of the Chicago Cubs (Photo by Justin Berl/Getty Images) /

1. Kyle Hendricks

The Yankees need a pitcher just like Kyle Hendricks.

This would be the splurge of all splurges from a trade package standpoint, but it’s truly the perfect move for the Yankees. Kyle Hendricks‘ style of pitching is a spot-on complement to the flame-throwing Cole and he’s signed through at least 2023 (with a vesting option for 2024). Here’s the contract breakdown:

2021: $14 million
2022: $14 million
2023: $14 million
2024: $16 million vesting option (or $1.5 million buyout)

Theo Epstein really worked his magic with this one because Hendricks is your prototypical No. 2 starter. He can pitch in big games. He can give you length. He’s efficient. He induces a lot of ground balls. He averages 7.6 K/9. He rarely ever blows up.

He’s 69-48 with a 3.12 ERA and 1.11 WHIP in 175 games since his debut in 2014. This contract takes him through his age-34 season and then the Yankees would rid themselves of his decline years. Hendricks behind Cole for the next four years is what will make this team a true contender because the Yankees’ offense always performs better when it’s relaxed.

If the lineup knows it has Cole and Hendricks on the bump twice in a series, the players won’t have to constantly come up with a big hit or feel the need to get on top early. It’ll just be business as usual. Let Cole be Cole. Let Hendricks be Hendricks. And let the offense do its damage when there’s an opening.

And you know what’s crazy? Hendricks has only been a top-three Cy Young finisher once despite sporting incredible FIPs since 2014 (3.32, 3.36, 3.20, 3.88, 3.78, 3.61, 3.55). Whether he brings home the hardware or not, this is a steady force that’s worth paying a high premium for.

The Cubs hold the power here, but the Yankees can very easily play into their needs and figure something out. If they were to consider that, this is an entirely different Yankees team.

CHICAGO, ILLINOIS - SEPTEMBER 26: Javier Baez #9 of the Chicago Cubs during the game against the Chicago White Sox at Guaranteed Rate Field on September 26, 2020 in Chicago, Illinois. (Photo by Quinn Harris/Getty Images)

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3 pitchers Yankees should absolutely overpay for in a trade